


Baby It's Cold Outside-- Hey, wait, where are you going?

by FoxVII



Category: Supernatural
Genre: Boss/Employee Relationship, Flirting, M/M, Miscommunication, it's as ethical as it can be though, lawyer!Sam, lawyer!gabe, office Christmas party
Language: English
Status: Completed
Published: 2019-12-23
Updated: 2019-12-23
Packaged: 2021-02-26 07:02:01
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,178
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21909394
Author URL: https://archiveofourown.org/users/FoxVII/pseuds/FoxVII
Summary: He wondered if he should regret speaking so casually to someone who could snap his fingers and ruin his career, but the anxiety train was cancelled as soon as Gabriel winked at him. Again.Or, Sam figures out that the office dick that's been following him around and insulting his boss...is, in fact, his boss' boss, slash older brother. And as it turns out, maybe Gabriel Novak isn't such a dick after all.
Relationships: Gabriel/Sam Winchester
Comments: 11
Kudos: 161





	Baby It's Cold Outside-- Hey, wait, where are you going?

**Author's Note:**

> Written for holydean as part of the Sabriel Secret Santa exchange for 2019! I hope you enjoy it!  
> Beta'd by the wonderful Amie! Thank you, my darling! <3

Sam started working at Novak and Novak LLC in September, fresh out of Stanford. The job was as challenging as Sam had expected, and in all the ways that he’d never would have seen coming. Sure, there were the long nights (obviously), difficult coworkers (sure) and the piles and piles of paperwork (definitely), but then there were the hours that he spent at his job where he ... wasn't actually doing his job.

He supposed that his circumstances were a bit unique in comparison to the usual first-year associate. Most of them (none of them, really) weren’t assigned to work directly under a name partner.

Sam’s good fortune made him the target of envy from the other associates in his year, his hours spent out of the office, dining with potential and current clients being seen as the height of success. There was no use explaining to them that those dinners were all hours that were being taken out of his precious bank of sleep, and that, honestly, he’d really rather be at home than in some upscale restaurant listening to a billionaire complain about how he didn’t have as much money as he wanted to have.

Thankfully, Castiel Novak seemed as ill-inclined towards these dinners as Sam was. He alternated between being cold and prickly, and occasionally veered toward the territory of outright hostile. With how often Sam found himself apologizing on his boss’ behalf, he suspected that if the firm wasn’t Castiel’s own, he never would have gotten his name on the door. 

But then again, maybe not. For all his lack of people skills, Castiel was - to put it simply - brilliant. He saw things in ways that other people simply couldn’t. And, remarkably still, considering his profession, he was honest. For a lawyer, Castiel was a terrible liar. And, likely, it was that open honesty and trustworthiness that he exuded that made him popular, and made his bluntness all that more tolerable.

Popular among clients, anyway. Less so around the office.

“Hardass, isn’t he?” 

Sam nearly fell off the ladder. He had thought he was alone in the firm’s library. He was halfway up one of the shelf ladders when the voice startled him out of his thoughts. He looked down to see a man standing at the foot of the bookshelf. 

Sam had seen him around the office - sharply dressed but somehow still casual, golden hair and eyes, and the easy kind of charming smile that made his stomach knot up - but they hadn’t been formally introduced. Given where his office was situated, Sam assumed that he was in management, but what he actually did was a mystery

“Pardon?”

“You’re Castiel’s associate, right?” he snorted. “He’s not exactly the easiest person to deal with.” 

Sam frowned to himself as he slid a book from the shelf, climbing down the ladder to face the man properly. “I don’t know about that,” he said. “I’d be cranky too if I knew I was the smartest person in the room, and probably the most overworked, at that.” Castiel had always been nice to him - or, well, his version of what counted as ‘nice’ - and it bothered Sam to hear people talk down about him. 

“Yeah? I think you’d be one of the only people to say that.”

“Maybe. But I don’t think anyone else really knows him well enough to talk.” He tucked away the ladder and gave the man another look. “Excuse me.” 

And then he left.

\---

Sam didn’t see the man again until it was October. He perched himself at the edge of the table, arms crossed over his chest as he glanced down at the papers spread over the desk. 

“What’s he got you working on?” 

Going off their last conversation, the ‘he’ was easy enough to guess. “Merger contract.”

The man hummed thoughtfully to himself. “He actually assigned you work? To do on your own?"

Sam shrugged. “Not entirely. It’s not like he isn’t looking it over afterwards.”

“Sure. But the last three associates he had, the only things he let them do were file papers or go on coffee runs. He's...a bit of a control freak."

Sam set his pen down with enough force to make it click against the table. “Okay, what's your deal with Castiel? What do you have against him?"

The man stared at him. "What do I have  _ against _ Castiel?"

"Yeah. What? Why are you always on his case?"

"On his case…?" The man blinked at him, and then a slow smile spread over his - annoyingly - handsome face. “ _ Oh _ . You don’t know who I am, do you?"

“Am I supposed to?”

The man’s smile grew, and he tapped the edge of Sam's open laptop. “Might want to check out our webpage, then. Surprised you didn’t already.” He stood, still grinning. “See you around, Sam.”

\---

Sam didn’t check right away, half-convinced that the guy was just looking to stoke his ego, or use him in whatever battle he had going on against Castiel.

Whatever was going on, Sam didn’t want to be in the middle of it. Never mind that he genuinely liked working for Castiel. It wasn’t like his boss was impossible to deal with. He wasn’t personable, no, and had exacting standards, but it was all for Sam's own good in the end. The advice that he got and the ways that he'd improved since starting at Novak and Novak LLC was all due to Castiel’s steady guidance.

But curiosity won out in the end, and he clicked onto the ‘meet the partners’ section of their webpage, and proceeded to choke on his coffee almost immediately.

He didn’t have to scroll far. Didn’t have to scroll at all, really. Because right at the top of the page was the guy’s picture, lips pulled into that handsome half-smirk of a smile that made him so irritating in the first place.

_ Gabriel Novak. _

The other Novak in Novak and Novak LLC, and Castiel’s brother.

As Sam wiped the coffee off his shirt, he got the distinct feeling that he was being tested all this time. 

Which. Sure. Fine. Sam was a brother too, he knew how it could be, with family. It wasn't as though he'd never gotten defensive over Dean. But...

How the fuck was he supposed to know if he  _ passed _ ?

\---

In hindsight, Sam should have guessed that it’d all go south during the office Christmas party.

_ I like working here, Dean, _ he'd said. 

_ Don’t embarrass me, Dean, _ he'd said. 

Why it never actually occurred to him  _ not _ to take his brother as his plus one…. Well. Evidently, for all his smarts, Sam Winchester wasn’t  _ that _ intelligent. 

Sure, he couldn’t predict the future and wouldn’t have known in advance that Dean would be three drinks in and draped all over his  _ boss _ , of all people, but he knew his brother. He could have guessed something.

And, well, yeah, Castiel  _ was _ handsome. He had a nice speaking voice, bright blue eyes, great build and adorably tousled hair. In any other circumstance Sam would have been proud of his brother’s taste (and the fact that he'd finally yanked his ass out of the closet).

The problem was that Castiel was his direct supervisor, his mentor at the law firm, and pretty much Sam’s gateway into getting ahead in his career. And Dean was alternating between being draped over his arm and pulling away to fold over laughing at something that couldn’t possibly be  _ that _ funny.

Castiel Novak was many things, yes. But what he  _ wasn’t _ was 'funny'.

Nevermind that Sam had his own problems. He hadn't managed to find Gabriel after he'd looked him up. Not knowing where he stood with the other man was putting him on edge. Castiel hadn't mentioned anything, though, so Sam assumed that everything was fine. That being said, it would have been nice to he able to make that certain for himself. 

“Well, would you look at that.” 

Sam jolted, head whipping around to look at the man that had suddenly appeared at his side.

“How do you manage to  _ do _ that?" he asked, because, just like all those times before, Gabriel had somehow managed to teleport beside him, without making a sound. 

"Do what? The charm and good looks are just natural, I'm afraid. Can't turn it off," he replied, easily. 

"I-- What? No. I just. Do you have a moment? I just wanted to… apologize. For before."

Gabriel arched a brow at him and swirled the champagne in his flute. "Cassie speaks highly of you, you know," he began. 

Over by the lounge chairs, Castiel’s secretary, Meg, dropped into the chair beside Dean and Castiel. Dean’s expression visibly soured, and the distance between his brother’s knee and Castiel’s immediately dropped from 5cm to 0. 

"He's smart, my brother. Real smart. But not always the best judge of character. And he's never complimented an associate of his before. I just wanted to see for myself if you were worth his attention." 

"And? I-- I mean. I was a bit of an asshole. To you."

The man’s eyes lifted from the spectacle, to Sam, and honestly what the fuck colour were they, even? Sam took a moment to wonder if he was even human, because human eyes did not come in the colour  _ gold _ , he was pretty sure. Brown? Yeah. Hazel? Sure. Gold? No, not unless the Novaks carried some fae blood in them.

“You gave me shit without knowing who I was, all to defend Castiel. I like that. And as you get to know me, you'll find that I rather like assholes," Gabriel told him, with a wink. 

And that...couldn't possibly mean….

Gabriel’s eyes drifted back to the couches where Meg now had her hand on Castiel’s opposite knee as she spoke animatedly. Dean had since glued himself up to Castiel’s side.

“That your date?” Gabriel asked, nodding at the live comedy special. Something had hardened in his gaze, some of that golden mirth retreating from the shine in his eyes.

“Dean? Oh--! No. Well, yes. I brought him. But he’s not my date-date. He’s my brother.”

The shimmer returned, as well as a playful grin. “Is that so? Well, no need for him to be left alone for so long, hm?” 

Gabriel snagged him by the wrist, dragging him over to where they were sitting. His hand was warm, his grip firm, and a different kind of warmth stole over Sam.

Unlike his brother, though, he had  _ some _ class. He could keep it together.

The firm had booked a lounge space for the party. It was dotted with plush, comfortable seating areas for guests to gather and converse, enough space to walk around and mingle, as well as for the servers to make their way around the room with drinks and appetisers. Sam nearly careened into one as Gabriel dragged him along, muttered a hasty apology and then made it to the couches.

“--And so I told him, if he wanted to see you that he’d have to just wait like everyone else,” Meg was saying. She’d leaned ever closer, dark-painted lips twisted with poorly concealed amusement. Dean was glaring at her hand, still. His own twitched on the back of the couch where he’d oh-so-casually slung it, allowing himself to be even closer. Any more and he’d be seated in Castiel’s lap entirely.

Sam knew Meg well enough to know that she had little romantic interest in Castiel. If anything, she'd spotted Dean's bullshit from across the room like they had, and was just making her own entertainment for the evening. He could take pity on Dean and let him know. He  _ could _ . 

But honestly, for getting sloshed and flirting with his boss, Dean could go ahead and suffer for a bit. He deserved it. 

Besides, Castiel didn’t look entirely  _ un _ comfortable to have Dean pressed as close as he was. If either of them bothered to have a conversation about it, they’d be able to work it out on their own, Sam was sure.

“How’s it hangin', Cas?” Gabriel said, by way of greeting, unceremoniously plopping himself down on the seat across from Castiel.

“It is hanging very well, thank you, Gabriel,” Castiel replied. Sam wondered if Castiel was actually humouring a penis joke, or if he had just missed it altogether. “And hello, Sam,” he added. 

Sam gave an awkward half-wave and carefully settled himself in beside Gabriel. He had half a mind to wedge in beside Dean and Castiel, but he figured that would be more trouble than it was worth. With a drink in his hand, anyway.

"Getting cozy with another name partner, are you, Sam?" Meg observed. Her voice was laced with its usual dry humour as she swirled the wine in her glass. "We'll have Winchester on our door at this rate." 

"I'm not really-- that's not-- I'm not  _ after _ that or anything." Now that he knew that he was in Gabriel's good graces, he didn't want any mistaken notions of ambition to ruin that. 

"Didn't think you were. But hey, if you got there on your own, that'd just be a reward for your hard work, wouldn't it?" Gabriel said.

Castiel nodded. "You're very skilled, Sam, and you learn well. They're good traits." 

“It’s snowing,” Dean observed, evidently in his own universe. He lifted a hand to haphazardly point at one of the windows. Fine flurries had started up, growing thicker by the minute. 

“Ah, I did hear that there was supposed to be something of a storm tonight. Depending on how far you live, you ought to get going. It’s been a late night as it is.” 

Dean looked from the window, back to Castiel. “Oh, that long? Feels like no time at all."

Sam groaned. Gabriel snickered. 

"Ah, they do say that thing about time flying."

"'They'," Gabriel teased, raising his fingers up to wag them around the word. And, ah, that's where Castiel must've gotten the air quotes thing. Unless his habit rubbed off on his elder brother instead. " _ You _ , on the other hand, are obviously an alien, and have never used an idiom in your life."

"If he's an alien then what does that make you?" Sam asked. He wondered if he should regret speaking so casually to someone who could snap his fingers and ruin his career, but the anxiety train was cancelled as soon as Gabriel winked at him. Again. 

And no, no warmth this time -  _ stop it, he's not attainable _ . 

"Wouldn't you like to know?" Gabriel replied instead, with all that good-natured humour that was making him a little too lovable for Sam's own good. 

"Did you drive here, Dean?" Castiel was asking. "I can call you a taxi. What's your address?" 

Dean grinned, that wide, slow smile pantydropper smile that Sam's known ever since Dean figured out how to use it in high school. "Why d'ya wanna know?"

"So that I can ensure that you get to your destination safe and sound," Castiel replied. 

The smile faltered. "Huh?" 

Gabriel leaned over to whisper something to his brother then sat back again, stretching his arm out over the couch back himself. 

"You know, it's getting pretty cold outside," he said, looking meaningfully at Sam. 

Sam drew out his phone, updating his weather app. "Oh, -10? That's not too bad." 

Gabriel blinked at him. "Not quite what I meant, Sam."

"Is there wind? That always makes it worse." Another refresh and glance. "Oh yeah, feels like -17 with the windchill. That's not fun." 

"I'm starting to understand why my brother gets along so well with you," Gabriel said, mostly to himself. "No I meant more that. It's cold outside. We should find a way to warm you up."

"I brought an extra scarf. Hey, did you already call for that Uber, Castiel? I can make sure Dean gets home safe. You shouldn't have to worry about that."

"It's no trouble, Sam. I'd rather you both make it home warm and safe. And Gabriel, I don't understand what you meant by 'watch and learn-'"

"Shh!" Gabriel hissed at him. 

Sam stood to pry a now-pouting Dean off his boss' side. "Thank you. I'll get him out of your hair now. It was nice seeing you again, Gabriel."

"Yeah, you too, Sam." 

\---

It wasn't until after holiday break that it hit him. 

Sam was halfway down the hall to Castiel's office when he turned on his heel mid-step and detoured over to Gabriel's. 

"You were flirting with me," he said, in lieu of a hello as he barged into his office. 

Gabriel stared at him, wide eyed. "I'll have to call you back," he said, into the receiver, and set down the handset of the desk phone. "Right. You finally caught onto that."

There was a brief moment of silence, before they both started to speak at the one time. 

"Yeah I-- I'm sorry. If we could have a do-over? I guess? That. Now that I know what's happening, I wouldn't mind-- And we can pretend that the entire thing didn't happen," Sam said, at the same time as Gabriel spoke:

"I may have also had a bit to drink. If you-- If that made you uncomfortable, I'm sorry. If you want, we can pretend that the entire thing didn't happen."

The ended in unison, and Sam's heart sank down to his stomach. 

"Wait. So you don't--?"

"You didn't--?"

"I didn't want--" 

"Okay, geez. This isn't working." Gabriel huffed a laugh to himself. "I meant that, you don't have to worry about anything. If you don't want to ever talk to me again, that's fine. And I promise you that your job here is secure. Shit, Cas'll have my head personally if I scare off the best associate that he's ever had." 

"That-- I was more worried that you didn't… mean it. I--" Sam took a deep breath, steadying his nerves. "Okay. I'd like it if you flirted with me again. And I'd like it a whole lot better this time, knowing what it is." 

Gabriel smiled, slow and easy, and gestured at the chair in front of him for Sam to sit down, which he did. "You know, I'm obligated to tell you that  _ you _ don't need to feel obligated to reciprocate." 

"I know. And I'm sure HR has forms for this."

"If not, they'll make them. And you're not in my direct purview anyway. I can promise that I won't have anything to do with your reviews. And if you ever want to leave, I won't make you sign a non-compete." 

Sam quirked a smile at him. "In that case...you know that sandwich shop down the street from here? You wanna get lunch?"

"The one that the weed guy sits in front of?" 

Sam gaped at him. "He's selling weed?"

Gabriel tilted his head at him - another gesture that he or Castiel must have inherited from the other - and then he laughed. "Oh, Sammich. Clearly Cassie's not been educating you properly. Don't worry. I'll teach you all the important things you need to know." 

**Author's Note:**

> You can also find me as fox-vii on tumblr!


End file.
